5-(1-Carbonyl-L-Trp)-2,2-dimethyl-[1,3]dithiolane-4-carboxylic acid

ID: ALA1681928

PubChem CID: 53319886

Max Phase: Preclinical

Molecular Formula: C18H20N2O5S2

Molecular Weight: 408.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)SC(C(=O)O)C(C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C(=O)O)S1

Standard InChI:  InChI=1S/C18H20N2O5S2/c1-18(2)26-13(14(27-18)17(24)25)15(21)20-12(16(22)23)7-9-8-19-11-6-4-3-5-10(9)11/h3-6,8,12-14,19H,7H2,1-2H3,(H,20,21)(H,22,23)(H,24,25)/t12-,13?,14?/m0/s1

Standard InChI Key:  XGKCODOSAXHQIK-HSBZDZAISA-N

Molfile:  

     RDKit          2D

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    0.7290    1.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7331   -0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9901    0.5674    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3442    0.5674    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497   -0.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4787   -0.5809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754   -1.5984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162   -1.6272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1319   -2.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227   -3.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1385   -3.7687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023   -3.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9746   -0.9351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569   -2.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727   -3.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441   -3.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597   -4.3522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -3.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682   -3.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1506   -4.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -3.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5866   -2.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8044   -2.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
  7  4  1  0
 13 14  1  0
 14 15  2  0
  4  8  1  0
 14 16  1  0
  9 17  2  0
  2  1  1  0
 13 18  1  1
  5  9  1  0
 18 19  1  0
 19 20  2  0
  3  2  1  0
  8 10  1  0
 20 21  1  0
 21 23  1  0
 22 19  1  0
  4  5  1  0
  8 11  2  0
 22 23  2  0
  5  6  1  0
 23 24  1  0
  6  2  1  0
 24 25  2  0
  9 12  1  0
 25 26  1  0
  2  7  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1681928

   5-[[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl]-2,2-dimethyl-1,3-dithiolane-4-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 408.50

Molecular Weight (Monoisotopic): 408.0814

AlogP: 2.32

#Rotatable Bonds: 6

Polar Surface Area: 119.49

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.56

CX Basic pKa: ┄

CX LogP: 2.04

CX LogD: -4.36

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: 0.00

References

1. Xu Y, Wang Y, Zhao M, Hou B, Peng L, Zheng M, Wu J, Peng S..  (2011)  Lead detoxification activities and ADMET hepatotoxicities of a class of novel 5-(1-carbonyl-L-amino-acid)-2,2-dimethyl-[1,3]dithiolane-4-carboxylic acids.,  21  (6): [PMID:21316230] [10.1016/j.bmcl.2011.01.070]

Source

Source(1):

• Scientific Literature